As temperatures continue to dip, I can’t help but daydream about rotting on my couch in a pair of snug sweatpants. But let’s face it: I’ve got things to do and places to be. Between festive holiday parties and late-night dinners, my social calendar is jam-packed, so I’m in desperate need of cold-weather going-out outfits that are equal parts warm and chic. Lucky for me, the celebrity crowd is brimming with style inspiration.
Take a look at Kendall Jenner’s wardrobe, for example. The model has plenty of looks worth copying year-round, but there's one leather jacket ensemble from several months ago that I can't stop thinking about: Styled with sleek trousers, pointy pumps, and a satin bag, she proved that sometimes, less is indeed more. Another one of my favorite celebrity going-out outfits comes courtesy of Zoë Kravitz at the Saint Laurent Spring 2026 show, where she endorsed the pencil skirt trend with a lace-trimmed version, paired with a buttoned windbreaker and playful heels. And you better believe I'm pinning Gabrielle Union's recent knit dress, a suede overcoat, and cherry red heels combo to my mood board.
Ahead, discover 8 cold-weather going-out outfit formulas I'm borrowing from the best-dressed A-listers this fall and winter. From relaxed uniforms fit for casual occasions to elevated ensembles meant for classy moments, you’ll find everything you could possibly need to recreate them, too, below.
Coat + Mini Skirt + Boots
For a recent girls’ night out with Gigi Hadid, Taylor Swift kept warm in a cozy pea coat adorned with charming buttons and sharp lapels. The singer ditched pants for a thigh-skimming mini skirt, and finished off her look with snakeskin boots and a crossbody bag. Borrow this simple three-part outfit for your next upscale dinner or cocktail lounge hang with the gals.
Cropped Jacket + Pencil Skirt + Heels
Considering the pencil skirt trend this season? Look no further than Kravitz's recent fashion week fit. By combining a sporty windbreaker with a sophisticated slip skirt, her outfit felt balanced, and versatile enough to go from day to night. Her look is anchored in a pair of barely-there sandals, but I’d swap those out for sturdy boots instead.
Leather Jacket + Trousers + Handbag
You can always count on Jenner to deliver a minimalist outfit rooted in a low-effort, high-reward appeal. All you’ll need is a black leather jacket, white pants (yes, you can—and should—wear them after Labor Day), slingbacks, and a handbag to cop her look.
Cardigan + Boots + Handbag
Hadid demonstrates that a lengthy cardigan can easily cosplay as an evening-friendly dress. Zhuzh up the look with textured boots and a leather bag, and you’ve got yourself an outfit that’s worthy of being worn on repeat. Just don’t forget to layer up with a long-sleeve shirt and a skirt—you want to look cute, not cold!
Chore Coat + Wide-Leg Jeans + Booties
Rihanna has a knack for making laid-back outfits feel effortlessly put-together. Here, she chose a pair of baggy denim bottoms and a billowing chore coat, further enhanced by wide-frame sunglasses, shimmering jewelry, a lustrous bag, and heels. It's all about easy layers and key accessories that level up your look.
Leather Jacket + Sheer Shirt + Jeans
The delicious chocolate brown color trend isn’t going anywhere, so you might as well incorporate this shade into your rotation of going-out outfits, if you haven't already. Do just that with a boxy leather jacket and a matching sheer top, à la Selena Gomez.
Turtleneck Dress + Overcoat + Heels
Thanks to Gabrielle Union, I found my next holiday party look. While the gray knit dress and black coat are low-key, the cherry red shoes add an unexpected pop of color. I’ll be following Union’s lead with the chic pieces below.
Leather Jacket + Leather Dress + Slingbacks
Styling an all-leather outfit might seem a bit intimidating, but allow Hailey Bieber to streamline the process for you: Simply reach for a sculpted dress, a roomy leather jacket, and ladylike slingbacks.
